How To Break In Your First Pair Of Red Wing Boots

How To Break In A New Pair Of Boots With Zero Pain

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Four years ago, @Ruaridhnicoll penned a column in The Guardian about a two-decades long obsession with Red Wings (he owns 11 pairs of the company’s infamously well-constructed and tough to break-in boots). After buying his first pair, they became the yardstick for every other similar product he owned. (Once you own a Rolex, a lot of watches look like toys — that kind of thing.)

A year after reading it, as Red Wings grew popular as a defacto celebration of “made in America,” we got our first pair: the 1907s. A heady copper color, a project to break in, and beautifully designed, all the same. After a couple wears, we realized we bought them too big (a classic mistake) and sold them — better on someone else’s feet. (Resale on Red Wings, like anything well-made, is exceptional.)

That is part of the boot maker’s charm (and frustration). Their boots, unlike, say, Helm’s, don’t fit true to size. There’s your shoe size, then your Red Wing Heritage size. If you’ve ever lusted after a pair, either for their longevity or comfort, you need to know yours, along with what the break-in process actually looks like, blisters and all. Here, we connect with people who wear them and the company itself to understand how to break in boots that’ll last you a lifetime.

Finding Your Size And Style

We visited the Red Wing Heritage brand store off Newburgh St. last month in Soho. It’s dimly lit and woody, a modern day saloon with boots instead of bourbon. The owner wears heritage worker chinos, a vest and a well-loved pair of Iron Rangers — one of the brand’s signature boots, notoriously difficult to break-in (wearing them new is like subjecting your feet to time in a Gulag). Inside, talk is of boots and only boots. Customers come and go over 45 minutes. Most have no problem spending hundreds of pounds on shoes, as easily as if they were buying a cup of coffee.

As part of the fitting process, we try on two pairs of the 877s — the brand’s signature 8-inch boot, and perhaps the one for which they are most famous. Normally, we take a size US11. Religiously, actually. Not so for Red Wings. In the Moc toe style (Red Wing offered to have us test these for the purposes of writing this article), we try a 10 and 10.5. This is an important decision about fit. How tight is tight? And how painful do you want that break-in process to be? Get your feet measured up before going further.

People who’ve worn Red Wings for years, credible people, will say, “get your Red Wings as tight as you can stand out of the box.” In our opinion and the opinion of one of the shopkeepers at Red Wing, this isn’t always true. Never leave the store with a size that hurts your feet, to the point that you’re unable to wiggle your toes. (Also, keep in mind the fit on each of Red Wing’s boots is different; just because you downsize 0.5 on a “moc toe,” doesn’t mean that’ll apply across the board on all styles). Sure, the leather gives, but don’t bank on that happening to the point of a comfortable fit. The blisters (and damage to your feet) aren’t worth it, no matter how good looking they are on foot.

“My number one recommendation,” says Andrew Brodrick, co-founder of Freenote Cloth, whose company often collaborates on product with Red Wing Heritage, “is always try on before you buy.” In an email to us about the boots, which are featured in all of the company’s marketing, he talks about the conscientiousness of Red Wings: how they exemplify a passion for minimalism. And how each person who works at Freenote wears Red Wings every day.

“I prefer to have my Red Wings just a tad small to allow the leather to mold properly to my feet. It’s tough for the first week when a little small, but better for the lifetime. Also (and this is important) big boots can look like clown shoes, so yeah, another reason to go a little small,” he adds. Ideally, with a purpose-built boot, it’ll feel a bit narrow to start, but never so narrow or tight that wearing them leaves you in pain.

Breaking Them In: A Step-By-Step Guide

Satchel B. Moore is Red Wing’s Community Manager based out of Minneapolis–Saint Paul. He has spent a long time thinking about, researching and engaging with people who love Red Wing boots. He explains that all of the company’s boots take some time breaking in, though some, like ours, are easier than others on account of their leather. Beckmans and Iron Rangers, as mentioned, will take a little more patience. Here are his step-by-step instructions on breaking in your first (or newest) pair.

“Pick a style you love, want to wear and that meets your needs. This is most important when it comes to soles, (A Nitrile Cork sole does amazingly well on concrete or indoor surfaces while the Lug Sole is best for outdoor applications). The same is true of the leather: muleskinner requiring less care than a smooth-finished leather to maintain its initial appearance.”

“Make sure they fit. No slipping. Tie them tight to keep your heel down. Again, snug and slightly narrow is ideal. They will stretch widthwise. Never buy a boot that is too short.”

“Wear them inside a bunch to REALLY make sure they fit [this tip worked wonders for us]. No one wants to buy a pair of boots someone wore to work one day only to decide they were the wrong size. Do this for your own peace of mind.”

Wait for it... “Wear them. Thick socks help with sore feet,” he says.

After about 100 wears, if they get very wet, very dirty or you feel like it: wipe them clean with a wet rag. Apply your favorite Red Wing Leather Care (plain old Mink oil works just the same) product. Let it set. Wipe off. Polish if you wish. Your boots are pretty tough and that leather is amazing, but they aren’t invincible.”

Our Opinion

The 877s, with their pale whisky-colored legacy leather, are intoxicating from the moment you take them out of their red and brown box. Their quality is obvious. As Moore puts it, they’re “a symbol of the good in America, the way few things are.” Just looking at them in your hall will make you want to head out and chop down a tree or walk in tall grass. The sole is stiff and uncompromising and the width fits snug, but our expectation is that, over time, this’ll improve.

So do they live up to their billing? The timelessness for which this style’s been known since 1953? Our verdict: yes. Their craftsmanship is apparent and, as creases start to form in their oil-tanned leather, their fit slowly improves, even after 20 hours of wear. Like everything well-made, buying your “size” is critical to ensuring you own a pair of icons you will seriously love.

Do they hurt at first? A bit. But we can already tell it’s worth it.

Mark Cohen has held strong opinions about style and sport since the start of his writing career. This has only worsened over time. He is a contributing writer to AskMen currently living in the U.K. Connect with him on Instagram or Twitter @mcohensays.

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